The Top 20 Celebrity Cameos In The History Of The Simpsons

During its 29-season run so far, The Simpsons has become famous for its frequent celebrity cameos. It feels like the majority of its episodes feature the voice of at least one notable star – sometimes more! In the most recent season alone, Game of Thrones star Nikolaj Coster-Waldau, Crazy Ex-Girlfriend lead Rachel Bloom and superstar singer Ed Sheeran have all cropped up in episodes, amongst many other celebs!

Still, not every Simpsons celebrity cameo is equally hilarious. While some have gone down in the show’s history as iconic moments or episodes, others have fallen flat and been forgotten. If you’re wondering which of the hundreds of Simpsons guest spots are the ones that are worth watching, don’t worry – we’ve got you sorted! Here are our top 20 best celebrity cameos in the show’s history.

20. Leonard Nimoy as himself

Star Trek actor and general sci-fi legend Leonard Nimoy made two equally memorable cameos as himself back in the golden ’90s era of The Simpsons. He first cropped up in the legendary episode “Marge vs. the Monorail,” a musical extravaganza about Springfield’s newest transport system. Nimoy crops up for the train’s maiden voyage, before beaming away Spock-style. Rather fittingly, he next made an appearance in an episode all about aliens! Well, kind of. The extraterrestrial in question turned out to be Mr. Burns. Still, it was all really an excuse to get Nimoy to lead a rousing sing-song in the woods! He also narrates the whole episode, but the singing is a bit more memorable.

19. Kelsey Grammer as Sideshow Bob

Frasier actor Kelsey Grammer is up there among the stars who have made the most cameos in The Simpsons. He’s appeared as clown-turned-criminal Sideshow Bob in no less than twenty episodes… Yet his character still hasn’t achieved his ultimate goal of killing Bart. For an intelligent guy, Bob is a pretty inept murderer! While all of Grammer’s cameos in the show have been hilarious, the highlight has to be the eighth-season episode “Brother From Another Series.” Grammer’s on-screen brother from Frasier, David Hyde Pierce, showed up to play Bob’s brother Cecil. What could’ve been a tacky reference to another hit show turned out to be a top-notch Simpsons classic.

18. Dustin Hoffman as Mr. Bergstrom

Who didn’t have a crush on a cute teacher at some point during their school years? Even the usually unflappable Lisa Simpson was left swooning thanks to Mr. Bergstrom, a sub brought in when Miss Hoover contracts Lyme disease. Mr. Bergstrom’s inspiring teaching methods, general friendliness, and silky voice led to Lisa – and all of us, to be honest – falling a little bit in love. Speaking of that voice, it didn’t belong to just anyone. Hollywood star Dustin Hoffman lent his voice to the character for one episode only. However, his involvement was kept secret at first: the actor initially used the pseudonym Sam Etic in the credits! The truth came out eventually, though, and everyone realized that they really DID recognize that voice from somewhere.

17. Kim Basinger and Alec Baldwin as themselves

Remember when Hollywood big-wigs Kim Basinger and Alec Baldwin were a happily married couple? They were one of the biggest power couples of the ’90s! In fact, they were so famous back then that they made a joint cameo on The Simpsons! That’s when you know you’ve made it, am I right? Baldwin and Basinger turned up as fictionalized versions of themselves in the season ten episode “When You Dish Upon a Star.” The Hollywood stars hide out in Springfield to avoid the pressures of L.A. life, hiring Homer as their assistant. Things go predictably wrong, as you’d expect when Homer is given any shred of responsibility. Poor guy.

16. Ron Howard as himself

In the very same episode that features Alec Baldwin and Kim Basinger becoming victims of Homer’s stupidity, acclaimed director Ron Howard doesn’t fare much better. The fictionalized Howard is visiting the celeb couple when they hire their new assistant, and he finds himself caught up in one of Homer’s hair-brained schemes. In fact, Howard ends up severely injured after a high-octane car / portable museum chase. Hearing Kim Basinger scream “YOU KILLED RON HOWARD” is an iconic moment for any Simpsons buff. Still, the director ends the episode very much alive and a lot richer. He cashes in after stealing one of Homer’s ideas and using it for his latest blockbuster. We kinda wish a movie about a “killer robot driving instructor that travels back in time for some reason” actually existed.

15. Stephen Hawking as himself

As one of the most eminent astrophysicists in the world, you wouldn’t think that Stephen Hawking would have the time to make a cameo in an animated American sitcom. However, he’s appeared in The Simpsons no less than four times to date! Since Hawking’s voice is famously computer-generated, there was no real need for him to turn up to the show’s recording studio – but he did anyway! Hawking reportedly wanted the authentic guest-starring experience. Simply sending a soundbite over wasn’t enough for him. The scientist has a famously keen sense of humor, and it shows in all of his guest appearances. He also manages to make everyone else in the world feel dumb even when he’s playing a fictional version of himself. It figures.

14. Aerosmith as themselves

The 1991 episode “Flaming Moes” is a bittersweet episode for any Simpsons fan. Sure, it led to us getting some of the best cameos in the show’s history… But poor Homer! His chance to make his fortune is cruelly snatched away by unscrupulous bartender Moe! Moe steals Homer’s idea for a killer cocktail – the Flaming Homer – and uses it to turn his bar into Springfield’s hottest venue. He becomes so successful that actual Aerosmith turns up to play at the bar! Sure, Steven Tyler gets the name of the town he’s performing in wrong, but it’s endearing in a rock-and-roll kinda way. Plus, the idea that the band can be bribed to play in a small-town bar simply with the promise of pickled eggs is a pretty entertaining one.

13. Conan O’Brien as himself

Fun fact: talk show star Conan O’Brien got his big break as a writer on The Simpsons! He penned classic episodes like “Marge Vs. The Monorail” and “Homer Goes To College” before leaving the show to start his on-screen career. Considering how important The Simpsons was to the early part of his career, it’s unsurprising that Conan later came back to make a cameo in the episode “Bart Gets Famous.” After Bart becomes a household name as the “I didn’t do it” kid on Krusty’s show, he does the talk show circuit, eventually ending up on Late Night With Conan O’Brien. While Bart’s time in the spotlight didn’t last, Conan’s brief cameo as a more arrogant version of himself has become a firm favorite amongst Simpsons fans.

12. Michael Jackson as Leon Kompowski

Whether Michael Jackson actually made a cameo on The Simpsons or not was a point of contention for many years. For a while, the evidence for and against was all very confusing. In the season three episode “Stark Raving Dad,” Homer meets a man named Leon Kompowski who genuinely believes that he’s actually Michael Jackson. He may not look like Michael, but he talks and sings like him. In the credits, Leon’s voice actor is named as “John Jay Smith.” However, a lot of MJ fans saw right through that pseudonym. Despite the producers of The Simpsons legally not being able to confirm John Jay Smith’s true identity for years, the fandom was convinced that Smith was actually the King of Pop. They were correct: in the DVD commentary for the season four episode “Itchy and Scratchy: The Movie,” the producers confirmed that Jackson really had voiced Leon.

11. Danny DeVito as Herb Powell

When the creators of The Simpsons decided to give Homer a long-lost brother, they set out to find a star prestigious and hilarious enough to voice such an important character. They found just that in Danny DeVito, who’s brought Herb Powell to life during two separate episodes. Herb was the product of a brief fling between Abraham Simpson and a woman named Gaby before Homer was born. After putting the baby up for adoption, Abe kept the existence of his first-born son a secret until he revealed the information to Homer mid-heart attack. Homer and Herb have a somewhat fraught relationship thanks to a bit of financial drama, but hey – all families have their issues! DeVito was supposed to reprise the role of Herb a few seasons ago, but that never materialized. Shame!

10. Michelle Pfeiffer as Mindy

While Homer and Marge Simpson generally have a pretty strong and happy marriage, their union has occasionally been severely tested over the course of the show. One such instance was in the season five episode “The Last Temptation of Homer,” in which Homer falls for his new colleague, Mindy Simmons. This donut-loving and incredibly alluring character was voiced by none other than Michelle Pfeiffer, who really made an effort to get into her new role. Mindy has a habit of drooling and gargling just like Homer, a noise that Pfeiffer initially found difficult to muster up. However, to get this aspect of the character just right, Pfeiffer put broccoli and water in her mouth! That doesn’t sound like the most pleasant gargling experience! Still, it was worth it: Pfeiffer’s guest spot is one of the most memorable out there.

9. Elizabeth Taylor as Maggie Simpson

As the youngest member of the Simpson family, Maggie has remained conspicuously silent for most of the show’s run. She is a baby, to be fair – she’s not had a chance to fully learn to talk yet! She probably never will, considering none of The Simpsons’ characters seem to age. At least the generally mute Maggie has managed to say one word in 29 seasons. In the episode “Lisa’s First Word,” the youngest Simpson manages to utter “Daddy” before dropping off to sleep. How sweet! To make this momentous occasion even more special, the show’s producers got legendary actress Elizabeth Taylor to record that simple line. Elizabeth Taylor! It was the cameo coup of the decade, to say the least.

8. Glenn Close as Mona Simpson

It’s kind of amusing just how many long-lost family members Homer Simpson has. He has his long-lost brother Herb, a British sister named Abbie, and an estranged mother who’d faked her own death! Homer’s mom Mona first appeared in the season seven episode “Mother Simpson,” blowing her cover to visit Homer’s grave after he, too, pretended to have passed away. Hollywood megastar Glenn Close was brought in to lend her voice to this infamous character, starring in three episodes until Mona died for real in “Mona Leaves-a.” Since then, Close has made two returns in dream sequences and hallucinations. The show loves her so much, they just can’t let her go! Admittedly, Mona is a pretty cool character. She’s a political activist whose last wish was to have her ashes scattered in a way that would destroy a plant pumping nuclear waste into the Amazon rainforest. What a badass!

7. Mark Hamill as himself

After the first trilogy of Star Wars movies concluded, Luke Skywalker actor Mark Hamill decided to turn his attention to voice acting. He managed to snag a guest spot in The Simpsons, portraying himself (and at one point playing the animated Luke Skywalker, as well). “Mayored to the Mob” has become a classic episode, in no small part due to Hamill’s appearance. It brought us one of the funniest exchanges in the show’s history – “Homer… use the…” “The Force?!” “No… the forks!” – and proved just how much Hamill is willing to laugh at himself. His fictionalized Simpsons counterpart is presented as a washed-up has-been who has to somehow incorporate Star Wars references into a production of Guys And Dolls. “Luke, Be A Jedi Tonight” is a banging tune, to be fair.

6. Buzz Aldrin as himself

You know your animated comedy show is a hit when you can persuade famous astronaut and second man on the Moon Buzz Aldrin to make a cameo as himself! Aldrin turned up in the appropriately space-themed season five episode “Deep Space Homer,” in which NASA decides to send the hapless Simpson into space. This is obviously a dreadful idea, and Homer’s incompetency makes the mission a tad more difficult than it should have been. Aldrin is perpetually frustrated at his inept colleague – as you would be, really – especially when Homer lets an entire bag of potato chips loose in zero-gravity conditions. Poor fictionalized Buzz doesn’t get an easy ride of it in his episode, but it’s hilarious nonetheless.

5. James Woods as himself

Rather bizarrely, actor James Woods briefly joined the cast of The Simpsons as the new owner of the Kwik-E-Mart! Yep – an actual Hollywood star took over from Apu for a while. It was a seemingly random choice, but one that ultimately worked quite well. After Apu is fired for selling Homer some spoiled meat, Woods is drafted in mainly for selfish reasons. The actor is preparing to portray a convenience store clerk in his next movie and wants to get some real-life experience of the job. Talk about method acting! Woods turns out to be less than great at serving customers, and confuses many patrons of the store when he asks them to ‘do the scene again.’ Er… You’re not actually in a movie at that point, James! This hilariously exaggerated fictional version of Woods was a joy to behold, even if it was just for one episode.

4. Patrick Stewart as Number One

As guest appearances go, acclaimed actor Patrick Stewart’s has to be one of the creepiest. Despite seeming like a pretty nice guy in real life, Stewart freaked us all out as Number One, the head of a Freemasons-esque society that Homer joins in The Simpsons’ sixth season. Number One is a frankly alarming character who seems to enjoy torturing his society’s new recruits. His imposing voice and extravagant dress sense only add to his generally sinister air. Still, the show’s producers couldn’t resist including one pretty amusing element in Number One’s character: at his day job, he works in a Star Trek museum! Stewart, of course, famously portrayed Captain Jean-Luc Picard in Star Trek: The Next Generation. It’s great when The Simpsons includes little fourth-wall-challenging in-jokes like that…

3. Meryl Streep as Jessica Lovejoy

While Meryl Streep is (rightfully) most famous for her Oscar-winning skills and generally incredible acting ability, her guest spot on The Simpsons is worth some attention too! For one episode only, Streep portrayed Jessica, the wayward daughter of Reverend Lovejoy. Jessica may look sweet and innocent on the outside, but she’s actually a devious rebel who loves nothing more than to stir up trouble. Of course, this leads to Bart falling head-over-heels in love with her, and Jessica actually becomes his first girlfriend! Streep played this two-faced character to perfection – we kinda wish the show would bring her back, at least for one more episode! However, Jessica’s antics were too extreme even for Bart, and he tends to just avoid her now. Fair enough.

2. The living members of The Beatles as themselves

Rather impressively, the producers of The Simpsons have managed to secure three out of the four Beatles guest spots on their show over the years! John Lennon was sadly long-gone before the show was even conceived. However, George, Ringo, and Paul have all cropped up over the years. The now-late George Harrison made an appearance in the classic episode “Homer’s Barbershop Quartet,” although Homer was more interested in eating brownies than actually talking to this world-famous musician. Paul McCartney showed up in the episode “Lisa the Vegetarian” to encourage the young Simpson in her meat-free ways, while Ringo Starr writes Marge Simpson a reply to one of her teenage fan letters. Each appearance was unique and tailored to the Beatle in question, but they were all equally hilarious.

1. Winona Ryder as Allison Taylor

Winona Ryder was one of the most famous actresses of the 1990s, so it’s unsurprising that she was invited to lend her voice to a Simpsons character! She portrayed one of the few characters to ever make the generally fabulous Lisa Simpson feel inferior: child prodigy Allison Taylor. While Lisa and Allison initially became friends, things became awkward when the latter began to outshine the former in pretty much every regard. Allison was an excellent scholar, a talented saxophone player, and a generally smart cookie. The two girls’ rivalry reached a head at the annual school diorama contest, although they managed to set aside their differences when they were both beaten by Ralph Wiggum. Although Lisa and Allison promised each other that they’d be best friends forever, Ryder hasn’t yet returned to the show. She’s probably too busy totally nailing her role on Stranger Things!

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